Epimerization-Free C-Terminal Peptide Activation

• Published in: Chemistry : a European journal Vol. 19; no. 50; pp. 16934 - 16937
• Main Authors: Popovic, Stanimir, Bieräugel, Hans, Detz, Remko J., Kluwer, Alexander M., Koole, Jelmer A. A., Streefkerk, Dieuwertje E., Hiemstra, Henk, van Maarseveen, Jan H.
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 09.12.2013; WILEY‐VCH Verlag; Wiley; Wiley Subscription Services, Inc
• Subjects: Activation; Amino Acid Sequence; aminolysis; aryl esterification; Carboxylic acids; Chemical reactions; Chemistry; Chemistry, Multidisciplinary; copper; Copper - chemistry; Esterification; Molecular Structure; Nitro Compounds; peptide activation; Peptide Fragments - chemical synthesis; Peptide Fragments - chemistry; Peptides; Physical Sciences; Science & Technology; Sulfhydryl Compounds - chemical synthesis; Sulfhydryl Compounds - chemistry; aryl esterification; aminolysis; 4-(METHYLTHIO)PHENYL; peptides; THERAPEUTIC PEPTIDES; COUPLING REAGENTS; CHEMOSELECTIVE LIGATION; POLYPEPTIDES; KINETICALLY CONTROLLED LIGATION; peptide activation; ESTERS; copper; CARBOXYLIC-ACIDS
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.201303347

Smooth operation: C‐terminal peptide activation with full stereointegrity was accomplished using a copper(II)‐mediated coupling reaction of carboxylic acids with arylboroxines (see scheme, NCL = native chemical ligation, Boc = tert‐butoxycarbonyl). This method allows epimerization‐free activation and ligation of peptides with racemization‐prone phenylglycine at the C terminus.